Besides an obnoxious sun, ornery dogs and the demanding terrain with more ups and downs than a ‘80s guitar solo, our biggest nemesis is the thorns. There are many, and, in turn, many flats.

After his fourth limp tire in just as many hours, Paolo Sangregorio, a 41-year-old angular graphic artist from Sweden, seems keen on tossing his Cannondale over the Meimoa dam on the outskirts of the Serra da Malcata Natural Reserve, where, until recently, roamed the exceptionally endangered Iberian Linx.

In the fifty-five miles of dusty track between Sortelha, another fine example of an ancient, castle-adorned hilltop village towering above golden plains and Almeida, I’ve, sigh, caught up to Paola in the flat department and the blackberry bushes that sport the thorns that are tormenting these tires have torn open my arms as I rip by them on my cushy dual suspension Gary Fisher in this generally sere countryside.

No vehicles are to be witnessed among the sun-bleached veldt and precarious rocky downhills are taken gung-ho, depositing me at the bottom wordlessly.

I’m elated to converse with a spirited 92-year-old still attending daily to his grazing livestock in the fields, too shy to let me capture his weathered complexion on my camera. Even the steamy bushwhack to find our crossing over the Coa River or this painful incline into Almeida, 15-kilometers (9.3 miles) from Spain, as the crow flies, can’t break my blithe spirit.

Sipping algid Super Brock's

Equally cheerful is Gary, who today, riding like Bugs Bunny on a latte binge, has already crested the summit and been sipping algid (cold) Super Brock’s for hours.

Breathless with roseate cheeks, I inquire whether he has explored this 18th-century stronghold that’s exceptionally maintained within towering walls that form a twelve-point star built to fend off the self-assured Spanish.

“Nope, just been chilling,” he responds, revealing his relaxed ways that, along with his gregarious personality, are quickly winning over his travel companions and the Portuguese alike.

Up and Down

Advancing to the South en masse, the Grande Rota is now taking us through a central plateau and the rough grounds of Serra da Estrela Natural Park where Iberian wall lizards, tawny owls and the occasional wolf mingle in the open air of the countries largest mountain range.

Past black oak and juniper, we ride though matter-of-course central Portugal villages like Moreirinhas, Carrapichana, Venda do Cepo, and finally, after a day with 1300 feet of lose dirt climbing, followed by a 1800-foot mind-blowing descent through the verdant Muxagata valley and another heart-pounding 1300-foot ridiculously vertical ascent of a boulder-strewn Roman path, a weary spandex-clad group pulls into Linhares da Beira.

An alley in Linhares

Once again, Gary is already there, ale in hand. The group is one lighter due to a busted-up ankle, the outcome of what is very much an arduous course.

A go-to spot for some of the big, blue marble’s best paragliders, Linhares rests on a slope keeping a watch over the Rio Mondego valley below.

“Matt, let’s go,” orders Carlos Vitorino, a 26-year-old tenacious Portuguese mountain biking virtuoso. It’s time for him to play and for me to shoot. For the next half hour or so he pedals almost effortlessly around the obstacles leading to the village castle, rambles down concrete steps attached to stone houses and fires off a few wheelies along the restored cobbled alleyways for the camera.

“Want me to do more?” His indomitable stamina is maddening. There are few residents to put up much of a fuss.

In fact, I’ve come to anticipate riding through these aged villages without much fanfare. It seems the young and ambitious have vacated the countryside seeking more prosperous fortunes in the country’s capital.

This has left only hard-as-nail seniors in this hardscrabble land to rise against the pace of the modern world. I wonder what will become of Linhares and other hamlets strewn across the central Portugal hills when they pass away. But for now, it’s wonderful to find spots unbent by tourism.

The village of Piadao

Haggard Yet Content

Fifty miles from Linhares is our terminus for today: Piódão. And, being nestled in the middle of three mountain ranges, there will be more climbing. Indeed, the first 10 kilometers (6.2 miles) of this atypical leaden-skied morning are just that.

At times the sand is six inches deep, making pedaling exhausting work, and other moments it’s just a sick steep grade.

I glance down at the GPS and sullenly watch the meters slowly creep by. Linhares is now just a speck on the forest fire ravaged landscape. Passing by wolfram mines employed by the British during the Second World War, I notice even Gary is struggling to keep his tires moving forward. As I alight from my bike to snap a picture of him laggardly riding by, he announces, “This is what it’s all about,” trying to keep his game face on.

Battle worn and ragged, I roll into the Vale do Rossim dam for lunch and masticate three ubiquitous ham and cheese sandwiches while languidly reclined in a hard plastic chair.

All dowhill from here

We’re encouraged to collect oak tree seeds that will be planted by a local NGO to help offset those that perished during recent forest fires in the mountainous Serre da Estrela region. But, weary, few can muster much more than a feeble attempt to be green.

“It’s pretty much all downhill from here,” Pedro C., an affable Lisbon native, briefs me as I slowly relieve a towering oak of some of its brown stringy buds. He wasn’t kidding.

The afternoon is spent with Shannon and Paolo inhaling dust as we navigate 4000 feet of descent along tight singletrack dotted with the occasional hair-raising asphalt.

“That is about my limit,” Paolo confesses after one section of particularly chancy trail. Just more training for the Grande Rota’s final challenge.

Seconds Please

The castle at Sabugal

Leaving Piódão, a particularly romantic village with brown slate homes meshed into the mountain like a Christmas tree and ablush by the rising sun, I conclude that with 55 miles and 10,000 feet of climbing among ridges and valleys, this will be one of the most epic rides of my thirty-three year existence.

A fitful sleep occurred, worrying about failed ascents, battered body parts and an unheroic van ride back to the start line. But these concerns do not come to fruition. Somehow, as if in some sort of medieval fairy tale, I arrive back at Castelo Novo unscathed and pumped to do more.

As if pedaling in the dirt among a sea of varicolored misty mountains, giant windmills dormant in the absent breeze and unique heritages never really happened today. While not always the reality during these past eight days, I stand here not with unalloyed relief that it’s over, but heavy-hearted to be unclipping for the last time in this land of gentle ways.

That night while sipping port and sharing harrowing experiences with my new friends, Gary stands and brightly toasts his fellow adventurers.

“To those who took on this challenge and kicked it in the ass.” Challenge, yes. Kicking it in the ass? Often, it was the other way around.

Wanna Ride?

At the moment A2Z Adventures (email) (351-919-048-373) are the only company offering supported mountain bike trips along the Grande Rota das Aldeias Históricas.

The ride to Sortelha

Their short or long nine-day tour (1150 Euro) includes guides, van support, hotel accommodation, food, transfer to and from Lisbon and the use of a GPS system so you can spend more time enjoying the thrilling trails and less time wondering: "left or right?"

They also offer a year-round self-supported option (790 Euro) that includes all of the above except for the guides, for those looking for a little more independence.

Spring (April-June) and Fall (Sept-Oct) are the best months for cycling in central Portugal. The summer months are just too stinking hot.

Portugal remains one of Europe’s biggest bargains. Expect your Euro to go further here than in other nearby countries.

Matthew Kadey is a Canadian-based photographer and freelance writer. Suffering from chronic wanderlust, he has cycled in several locales including Asia, Jordan, New Zealand, Belize, Ireland, Ethiopia and Hawaii. His photography and writing can be seen at mattkadey.ca.

Since 2000, GoNOMAD Travel has provided travelers with inspiring travel articles, photos from destinations around the world, and a community of like-minded travelers who are seeking to learn about the world and share their travels with others.